A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check availability on Winchester Hotels with Pool

Tonight
23 Sep - 24 Sep
Tomorrow
24 Sep - 25 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Winchester hotels with a pool

An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a small table.
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

1. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
  • Splash into luxury at this hotel's sparkling indoor pool, complete with plush sun loungers and serene atmosphere.
฿4,935
฿5,355 total
includes taxes & fees
24 Sept - 25 Sept
Best Western Plus Keene Hotel
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

2. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
  • Splash into comfort at this indoor pool oasis offering year-round aquatic escape in Keene.
฿4,637
฿5,031 total
includes taxes & fees
24 Sept - 25 Sept
Keene Elm City Hotel, an Ascend Collection Hotel
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

3. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
  • Relaxing indoor pool retreat with comfortable loungers sets the perfect stage for your Vermont ski getaway.
฿4,774
฿5,252 total
includes taxes & fees
28 Sept - 29 Sept
Comfort Inn & Suites Brattleboro I-91
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A lobby with wooden paneling, a fireplace, and two green armchairs.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.

4. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
  • Immerse in rejuvenating waters at this mountain-adjacent hotel featuring a pristine indoor pool and relaxing hot tub sanctuary.
฿4,525
฿4,977 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn Brattleboro
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A gym with treadmills, elliptical machines, and stationary bikes.
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

5. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
  • Splash into serenity at this inviting indoor pool hotel, where year-round swimming meets complete comfort and relaxation.
฿5,315
฿5,767 total
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn & Suites Keene
A swimming pool with a clear blue water, surrounded by lounge chairs and a lifebuoy on the wall.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

6. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
  • Splash into family fun with a year-round indoor pool perfect for kids at this rural Vermont retreat.
฿6,459
฿7,104 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A room with a dining table, chairs, a sofa, and a red carpet leading to a door.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

7. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
  • Refresh poolside with a seasonal summer dip at this Vermont motel for adults only.
฿3,294
฿3,623 total
includes taxes & fees
22 Oct - 23 Oct
Econo Lodge Brattleboro South
A swimming pool with lounge chairs and a covered umbrella.
A cozy reading area with wooden chairs, a table with newspapers, and potted plants.
A hotel with a clock tower, a parking lot, and a well-maintained garden.
A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.

8. Black Mountain Inn

Black Mountain Inn
Brattleboro
  • Refreshing poolside retreat in Black Mountain with seasonal swimming and scenic garden views.
฿5,031
฿5,534 total
includes taxes & fees
27 Sept - 28 Sept
Black Mountain Inn
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

9. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
  • Dive into the year-round aquatic escape at this art deco hotel with a pristine indoor pool.
฿7,205
฿7,818 total
includes taxes & fees
30 Sept - 1 Oct
Courtyard by Marriott Keene Downtown
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.
A living room with a fireplace, a pool table, and comfortable seating.
A dining area with a round wooden table, white chairs, and a green wall.

10. Inn on Putney Road

Inn on Putney Road
Brattleboro
  • Tranquil outdoor pool retreat complements this historic bed & breakfast with garden views and mountain adventures.
฿12,025
฿13,228 total
includes taxes & fees
24 Sept - 25 Sept
Inn on Putney Road
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Winchester Hotel Reviews

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Bed was very comfortable, shower clean and had good water pressure. Didn’t spend much time there. Checked in at 4:00am and they gave us late check out at noon."
Pamela 1-night trip
Posted 1 day ago
Hampton Inn & Suites Greenfield
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Great! Clean, comfortable, friendly staff!"
Noelle 1-night trip
Posted 3 days ago
Best Western Plus Keene Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast room was great"
bonnie 1-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Though it's not a luxury hotel, the staff is exceptionally nice & helpful. the property is clean, there are carts for moving luggage, the breakfast service is fine. It's quiet. the bathroom is spacious w.nice towels & toiletries. Parking is easy."
Robert 1-night trip
Posted 5 days ago
Comfort Inn & Suites Brattleboro I-91

Frequently asked questions

What are some accommodation options with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Colonial Motel: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Latchis Hotel: Features buffet, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel: Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Gardner Inn: Features buffet, an indoor pool and free self parking.
What is there to see and do in Winchester?
Make a point to visit attractions such as Birch Point and Rhododendron State Park. During your stay, visit sights such as Winchester Speedpark, New England Sweetwater Farm & Distillery and Pisgah State Park. Take in the natural beauty of Winchester with the lakeside setting.
When is the best time to book a hotel with a pool in Winchester?
Taking the local weather in Winchester into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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